Mono- and bivalent ligands bearing mannose 6-phosphate (M6P) surrogates: Targeting the M6P/ insulin-like growth factor II receptor

David B. Berkowitz, Gourhari Maiti, Bradley D. Charette, Christine D. Dreis, Richard G. MacDonald

Research output: Contribution to journalArticle

40 Scopus citations

Abstract

(Chemical Equation Presented) Mannose 6-phosphate mimics locked into the α-configuration and bearing hydrolase-resistant phosphate surrogates were synthesized and evaluated for binding affinity to the mannose 6-phosphate/insulin-like growth factor II receptor (M6P/IGF2R). Affinity increases as the phosphate surrogate is varied in the order malonyl ether < malonate < phosphonate. An alkene cross-metathesis approach to sought-after bivalent M6P-bearing ligands is also described. These compounds were designed to map onto biantennary sectors of high-mannose-type oligosaccharides carried by glycoprotein M6P/IGF2R ligands.

Original languageEnglish (US)
Pages (from-to)4921-4924
Number of pages4
JournalOrganic Letters
Volume6
Issue number26
DOIs
StatePublished - Dec 23 2004

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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